Formation of 3-(m-chlorobenzoyloxy)-2-(phenylseleno)propan-1-ol and 2- (m-chlorobenzoyloxy)-3-(phenylseleno)propan-1-ol from a reaction of allyl phenyl selenide with m-chloroperoxybenzoic acid

Tetrahedron Letters

Volumn 39, Issue 48, 1998, Pages 8877-8880

  Hirose, Takanori ^a   Morita, Nobuhiro ^a   Asakura, Mitsuhiro ^a   Kitahara, Keisuke ^a   Toyota, Shinji ^a   Oki, Michinori ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; ORGANOSELENIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032569865     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02020-6     Document Type: Article

References (16)

1. 1. Reich, H. J. "[2,3]Sigmatropic Rearrangements of Organoselenium Compounds" in Liotta, D. ed., "Organoselenium Chemistry", John Wiley, New York (1987).
2. 2. Nishiyama, H.; Itagaki, K.; Sakuta, K.; Itoh, K. Tetrahedron Lett., 22, 5285 (1981).
3. 3. a) Clive, D. L. J. Tetrahedron, 34, 1049 (1978):
4. b) Duddeck, H., Wagner, P.; Rys, B. Magn. Reson. Chem., 31, 736 (1993).
5. -1.
6. -1; R = 0.056, Rw = 0.086.
7. AB = 11.2 Hz), 3.75-3.83 (1H, m), 7.26-7.28 (3H, m), 7.52-7.55 (2H, m).
8. 8 in the presence of m-chlorobenzoic acid gave compounds 4 and 5 as overwhelming products under the conditions used.
9. 8. Hori, T.; Sharpless, K. B. J. Org. Chem., 43, 1689 (1978).
10. 9. Ionization potential of dimethyl selenide is 8.40 eV [Cradock, S.; Whiteford, R. A. J. Chem. Soc., Dalton Trans. 2, 68, 281 (1972)], whereas those of terminal olefins are 9.5-9.7 eV [Turner, D. W. Adv. Phys. Org. Chem., 4, 31 (1966)].
11. 9. Ionization potential of dimethyl selenide is 8.40 eV [Cradock, S.; Whiteford, R. A. J. Chem. Soc., Dalton Trans. 2, 68, 281 (1972)], whereas those of terminal olefins are 9.5-9.7 eV [Turner, D. W. Adv. Phys. Org. Chem., 4, 31 (1966)].
12. 10. Sharpless, K. B.; Lauer, R. F. J. Org. Chem., 37, 3073 (1972).
13. 11. Swern, D. "Organic Peroxy Acids as Oxidizing Agents, Epoxidation", Swern, D. ed., "Organic Peroxides", Vol. 2, Chapter V, pp. 355-533, Wiley, New York (1971): Berti, G. Top. Stereochem., 7, 93 (1973).
14. 11. Swern, D. "Organic Peroxy Acids as Oxidizing Agents, Epoxidation", Swern, D. ed., "Organic Peroxides", Vol. 2, Chapter V, pp. 355-533, Wiley, New York (1971): Berti, G. Top. Stereochem., 7, 93 (1973).
15. 12. Hanzlik, R. P.; Shearer, G. O. J. Am. Chem. Soc., 97, 5231 (1975).
16. 13. Reich, H. J.; Yelm, K. E.; Wollowitz, S. J. Am. Chem. Soc., 105, 2503 (1983).